CN117099507A

CN117099507A - Material for organic electroluminescent device

Info

Publication number: CN117099507A
Application number: CN202280023218.1A
Authority: CN
Inventors: 鲁文·林格; 米丽娅姆·恩盖尔; 塞巴斯汀·施托尔茨; 塞巴斯汀·迈耶; 拉拉-伊莎贝尔·罗德里格斯
Original assignee: Merck Patent GmbH
Current assignee: Merck Patent GmbH
Priority date: 2021-04-09
Filing date: 2022-04-06
Publication date: 2023-11-21
Also published as: KR20230169215A; WO2022214507A1; TW202309242A; EP4320649A1

Abstract

The present invention relates to a composition comprising a compound of formula (H1) and a compound of formula (H2). The invention also relates to a formulation comprising a composition comprising a compound of formula (H1) and a compound of formula (H2) and a solvent. Finally, the invention relates to an electronic device comprising such a composition.

Description

Material for organic electroluminescent device

The development of functional compounds for electronic devices is currently the subject of intensive research. In particular, the object is to develop compounds with which improved performance of electronic devices in one or more relevant respects, such as power efficiency and lifetime of the device and color coordinates of the emitted light, can be achieved.

According to the invention, the term "electronic device" refers in particular to Organic Integrated Circuits (OIC), organic Field Effect Transistors (OFET), organic Thin Film Transistors (OTFT), organic Light Emitting Transistors (OLET), organic Solar Cells (OSC), organic optical detectors, organic photoreceptors, organic Field Quench Devices (OFQD), organic light emitting electrochemical cells (OLEC), organic laser diodes (O-lasers) and organic electroluminescent devices (OLED).

Of particular interest is the provision of compounds for use in the last-mentioned electronic devices known as OLEDs. The general structural and functional principles of OLEDs are known to the person skilled in the art and are described for example in US 4539507.

Further improvements are needed with regard to the performance data of OLEDs, especially in view of a wide range of commercial applications, such as in display devices or as light sources. Of particular importance in this respect are the lifetime, efficiency and operating voltage of the OLED and the color values achieved. Particularly in the case of blue-emitting OLEDs, there is the potential for improvement in terms of efficiency, lifetime and operating voltage of the device.

An important starting point for achieving the improvement is the choice of the emitter compound and the host compound. In practice, the emitter compound is typically used in the light emitting layer in combination with a second compound that serves as a host compound or host compound. A light-emitting compound is herein considered to mean a compound that emits light during operation of an electronic device. In this case, the host compound is considered to mean a compound present in a mixture in a larger proportion than the emitter compound. The term matrix compound and the term host compound can be used synonymously. The host compound preferably does not emit light. Even if a plurality of different host compounds are present in the mixture of light-emitting layers, their respective proportions are generally greater than the proportions of the light-emitting compounds, or if a plurality of light-emitting compounds are present in the mixture of light-emitting layers, the respective proportions of the host compounds are greater than the proportions of the various light-emitting compounds.

Such embodiments have been described for a fluorescent light emitting layer, for example in US 4769292.

If a mixture of compounds is present in the light-emitting layer, the light-emitting compound is typically a component that is present in smaller amounts, i.e. in smaller proportions, than the other compounds present in the light-emitting layer mixture. In this case, the emitter compound is also referred to as a dopant.

Host compounds for fluorescent emitters known from the prior art are a variety of compounds. The light-emitting layer may comprise one or more host compounds. Known in the art are host compounds comprising a mixture of deuterated and non-deuterated host compounds (e.g. in WO 2020/080416).

However, there is still a need for other host materials or other combinations of host materials for fluorescent emitters that can be used in OLEDs and that result in OLEDs having very good characteristics in terms of lifetime, color emission and efficiency. More particularly, a host material or combination of host materials for fluorescent emitters is needed that combines a very high efficiency, a very good lifetime and a very good thermal stability.

Furthermore, it is known that OLEDs can comprise different layers, which can be applied by vapor deposition in a vacuum chamber or by solution treatment. Vapor deposition-based methods lead to very good results, but they can be complex and expensive. Thus, there is also a need for compositions comprising OLED materials that can be easily and reliably processed from solution. More particularly, there is a need for compositions comprising OLED materials that can be deposited as a uniform film during the manufacture of an OLED when processed from a formulation, more particularly from a solution such as an ink. In this case, the materials should have good solubility in the solution in which they are contained, and the deposited film containing the OLED material should be as smooth as possible after the drying step that results in removal of the solvent. Importantly, the deposited layer forms a smooth and uniform film because non-uniformity of layer thickness results in non-uniform brightness distribution, thinner film thickness regions exhibiting increased brightness and thicker regions exhibiting reduced brightness, which results in reduced quality of the OLED. At the same time, OLEDs comprising films treated from solution should exhibit good properties, for example in terms of lifetime, operating voltage and efficiency.

In addition, there is a need for a method of preparing stable OLED materials that are easy to purify and easy to process. There is a need to achieve economically and qualitatively interesting processes by providing OLED materials with acceptable purity and high yield.

The present application is therefore based on the technical object of providing a composition comprising an OLED material, which composition is suitable for use in an electronic device such as an OLED, more particularly as a matrix component of a fluorescent light emitter. The application is also based on the technical object of providing a composition comprising an OLED material, which is particularly suitable for solution treatment. The application is also based on the technical object of providing a method.

In the study of novel compositions for electronic devices, it has now been found that compositions comprising a compound of formula (H1) and a compound of formula (H2) as defined below are very suitable for use in electronic devices. In particular, they achieve one or more, preferably all, of the above technical objects.

The present application thus relates to a composition comprising:

a first host material of formula (H1),

A second host material of formula (H2)

And a dopant material;

wherein the coincidence and notation used applies as follows:

G ₁ is an aromatic or heteroaromatic ring system having from 6 to 60 aromatic ring atoms, which in each case may be bound by one or more radicals R ^X Substitution;

G ₂ a group selected from formula (G2):

wherein the group E is selected from-Y=Y-, -C (R ^B0 ) ₂ -、Si(R ^B0 ) ₂ -、-O-、-S-、-C(＝O)-、-S(＝O)-、-SO ₂ -、–BR ^B0 -、-N(R ^B0 ) -or-P (R) ^B0 ) Divalent bridging groups in-preferably Y=Y-, -C (R ^B0 ) ₂ -, -O-, -S-; and wherein R is ^B0 Identically or differently on each occurrence represents: h, F, CN, a linear alkyl group having 1 to 40C atoms or a branched or cyclic alkyl group having 3 to 40 atoms, each of which may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted in each case by one or more groups R; wherein two adjacent substituents R ^B0 An aliphatic or aromatic ring system, which may be mono-or polycyclic, which may be substituted by one or more radicals R;

y represents C-R identically or differently on each occurrence ^Y Or N; provided that when Y is the same as the group Ant ₂ Y represents C when bonded;

Ant ₁ is a group of formula (A1):

wherein the dotted bond in formula (A1) represents a group G ₁ In which the group Ant is ₁ Can be combined with G at any free position ₁ Bonding;

Ant ₂ is a group of formula (A2):

wherein the dotted bond in formula (A2) represents a group G ₂ And wherein the group Ant ₂ Can be combined with G at any free position ₂ Bonding;

Ar ^A1 、Ar ^B1 、Ar ^AS 、Ar ^BS identically or differently on each occurrence are aromatic or heteroaromatic ring systems having from 5 to 60 aromatic ring atoms, which may also be substituted in each case by one or more radicals R;

R ^A1 To R ^A8 、R ^B1 To R ^B8 、R ^Y 、R ^X Represents, identically or differently on each occurrence, a group selected from: h, D, F, cl, br, I, CHO, CN, C (=O) Ar, P (=O) (Ar) ₂ ，S(＝O)Ar，S(＝O) ₂ Ar，N(R) ₂ ，N(Ar) ₂ ，NO ₂ ，Si(R) ₃ ，B(OR) ₂ ，OSO ₂ R, a linear alkyl, alkoxy or thioalkyl radical having from 1 to 40C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40C atoms, which may each be substituted by one or more radicals R, where in each case one or more non-adjacent CH ₂ The radicals may be substituted by RC=CR, C≡ C, si (R) ₂ 、Ge(R) ₂ 、Sn(R) ₂ 、C＝O、C＝S、C＝Se、P(＝O)(R)、SO、SO ₂ O, S or CONR and wherein one or more H atoms may be replaced by D, F, cl, br, I, CN or NO ₂ Alternatively, having 5 to 6An aromatic or heteroaromatic ring system of 0 aromatic ring atoms, which in each case may be substituted by one or more radicals R, and an aryloxy group of 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R;

provided that R ^B1 To R ^B8 And R is ^Y Not representing D; and wherein two adjacent groups R ^A1 To R ^A8 、R ^B1 To R ^B8 、R ^Y Or R is ^X May together form an aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more groups R;

r, identically or differently at each occurrence, represents: h, D, F, cl, br, I, CHO, CN, C (=O) Ar, P (=O) (Ar) ₂ ，S(＝O)Ar，S(＝O) ₂ Ar，N(R') ₂ ，N(Ar) ₂ ，NO ₂ ，Si(R') ₃ ，B(OR') ₂ ，OSO ₂ R 'is a linear alkyl, alkoxy or thioalkyl radical having from 1 to 40C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40C atoms, which may each be substituted by one or more radicals R', where in each case one or more non-adjacent CH ₂ The radicals may be substituted by R ' C=CR ', C≡ C, si (R ') ₂ 、Ge(R') ₂ 、Sn(R') ₂ 、C＝O、C＝S、C＝Se、P(＝O)(R')、SO、SO ₂ O, S or CONR' and wherein one or more H atoms may be replaced by D, F, cl, br, I, CN or NO ₂ Alternatively, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which in each case may be substituted by one or more radicals R ', an aryloxy group having from 5 to 60 aromatic ring atoms, which in each case may be substituted by one or more radicals R'; wherein two adjacent groups R may together form an aliphatic or aromatic ring system, which may be substituted with one or more groups R';

ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which may also be substituted in each case by one or more radicals R';

r' represents identically or differently on each occurrence: h, D, F, cl,br, I, CN, a linear alkyl, alkoxy or thioalkyl radical having from 1 to 20C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 20C atoms, where in each case one or more non-adjacent CH ₂ The radicals may be replaced by SO, SO ₂ O, S, and wherein one or more H atoms may be replaced by D, F, cl, br or I, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms; and is also provided with

n is, identically or differently, 0 or 1 at each occurrence; wherein when n is 0, then the corresponding Ar is absent ^AS Or Ar ^BS And anthracene groups directly bonded to the group G ₁ Or G ₂ ；

m is 0 or 1;

characterized in that the compound of formula (H1) comprises at least one deuterium atom and the compound of formula (H2) is substantially free of deuterium atoms.

More preferably, the compound of formula (H2) does not contain deuterium atoms. Thus, the radicals R and R' do not represent deuterium atoms in the compounds of formula (H2).

Deuterium atoms are also referred to herein as "D".

Furthermore, the following definitions of chemical groups are applicable for the purposes of the present application:

in the sense of the present application, an aryl group contains 6 to 60 aromatic ring atoms, preferably 6 to 40 aromatic ring atoms, more preferably 6 to 20 aromatic ring atoms; heteroaryl groups in the sense of the present application contain 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, at least one of which is a heteroatom. The heteroatoms are preferably selected from N, O and S. This represents the basic definition. If other preferences are indicated in the description of the application, for example as to the number of aromatic ring atoms or heteroatoms present, these preferences apply.

Aryl groups or heteroaryl groups are herein considered to mean: a simple aromatic ring, i.e. benzene or a simple heteroaromatic ring such as pyridine, pyrimidine or thiophene; or fused (cyclized) aromatic or heteroaromatic polycyclic such as naphthalene, phenanthrene, quinoline or carbazole. In the sense of the present application, a fused (cyclized) aromatic or heteroaromatic polycyclic is composed of two or more simple aromatic or heteroaromatic rings fused to one another.

Aryl or heteroaryl groups which may in each case be substituted by the abovementioned groups and which may be attached to the aromatic or heteroaromatic ring system by any desired position are particularly understood to mean groups derived from: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chicory, perylene, fluoranthene, benzanthracene, benzophenanthrene, naphthacene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenoneOxazine, pyrazole, indazole, imidazole, benzimidazole, naphthazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole,/- >Azole, benzo->Azole, naphtho->Azole, anthra->Azole, phenanthro->Azole, i->Oxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2, 3-triazole, 12, 4-triazole, benzotriazole, 1,2, 3-/i>Diazole, 1,2,4->Diazole, 1,2,5->Diazole, 1,3,4->Diazoles, 1,2, 3-thiadiazoles, 1,2, 4-thiadiazoles, 1,2, 5-thiadiazoles, 1,3, 4-thiadiazoles, 1,3, 5-triazines, 1,2, 4-triazines, 1,2, 3-triazines, tetrazoles, 1,2,4, 5-tetrazines, 1,2,3, 4-tetrazines, 1,2,3, 5-tetrazines, purines, pteridines, indolizine and benzothiadiazoles.

An aryloxy group as defined according to the invention is taken to mean an aryl group as defined above bonded through an oxygen atom. Similar definitions apply to the heteroaryloxy groups.

An aromatic ring system in the sense of the present invention contains 6 to 60C atoms, preferably 6 to 40C atoms, more preferably 6 to 20C atoms in the ring system. Heteroaromatic ring systems in the sense of the present invention contain from 5 to 60 aromatic ring atoms, preferably from 5 to 40 aromatic ring atoms, more preferably from 5 to 20 aromatic ring atoms, at least one of which is a heteroatom. The heteroatoms are preferably selected from N, O and/or S. An aromatic or heteroaromatic ring system in the sense of the present invention is intended to be understood as meaning the following system: it is not necessary to contain only aryl or heteroaryl groups, but in the system a plurality of aryl or heteroaryl groups may also be linked by non-aromatic units (preferably less than 10% of the non-H atoms), such as for example: sp (sp) ³ Hybridized C, si, N or O atoms, sp ² A hybridized C or N atom, or an sp hybridized C atom. Thus, for example, systems such as 9,9 '-spirobifluorene, 9' -diarylfluorene, triarylamines, diaryl ethers, stilbenes and the like are also intended to be regarded as aromatic ring systems in the sense of the invention, in which two or more aryl groups are, for example, linear or cyclic alkanesThe same is true of groups, alkenyl or alkynyl groups or systems linked by silyl groups. Furthermore, systems in which two or more aryl or heteroaryl groups are connected to one another by single bonds are also understood to mean aromatic or heteroaromatic ring systems in the sense of the invention, for example systems such as biphenyl, terphenyl or diphenyltriazine.

An aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms which may in each case also be substituted by a group as defined above and which may be attached to the aromatic or heteroaromatic group by any desired position is in particular considered to mean a group derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chicory, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, diphenylene, terphenyl, benzidine, tetrabiphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, trimeric indene, spirotrimeric indene, spiroisoparaffin, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine Oxazine, pyrazole, indazole, imidazole, benzimidazole, naphthazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole,/->Azole, benzo->Azole, naphtho->Azole, anthra->Azole, phenanthro->Azole, i->Oxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazaanthracene, 2, 7-diazapyrene, 2, 3-diazapyrene, 1, 6-diazapyrene, 1, 8-diazapyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine>Oxazine, phenothiazine, fluororuber, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2,3->Diazole, 1,2,4->Diazole, 1,2,5->Diazole, 1,3,4->Diazoles, 1,2, 3-thiadiazoles, 1,2, 4-thiadiazoles, 1,2, 5-thiadiazoles, 1,3, 4-thiadiazoles, 1,3, 5-triazines, 1,2, 4-triazines, 1,2, 3-triazines, tetrazoles, 1,2,4, 5-tetrazines, 1,2,3, 4-tetrazines, 1,2,3, 5-tetrazines, purines, pteridines, indolizine and benzothiadiazoles.

For the purposes of the present invention, wherein the other individual H atoms or CH ₂ The straight-chain alkyl groups having 1 to 40C atoms or branched or cyclic alkyl groups having 3 to 40C atoms or alkenyl or alkynyl groups having 2 to 40C atoms, which groups may be substituted by the abovementioned groups mentioned under the definition of the groups, are preferably taken to mean the following groups : methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl. Alkoxy or thioalkyl having 1 to 40C atoms is preferably taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctyloxy, 2-ethylhexoxy, pentafluoroethoxy, 2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio tert-butylthio, n-pentylthio, zhong Wuliu, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2-trifluoroethylthio, vinylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, acetylenylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or Xin Guiliu.

For the purposes of the present invention, the term that two or more groups may form a ring with each other is intended to be taken to mean in particular that the two groups are connected to each other by a chemical bond. This is shown by the following scheme:

however, in addition, the above expression is also intended to be taken to mean that, in the case where one of the two groups represents hydrogen, the second group is bonded at the bonding position of the hydrogen atom, thereby forming a ring. This is shown by the following scheme:

when two groups form a ring with each other, then it is preferred that the two groups are adjacent groups. Adjacent groups in the sense of the present invention are groups which are bonded to atoms directly connected to each other or to the same atom.

According to a preferred embodiment, the molecular weight (Mw) of the compound of formula (H1) is Mw.gtoreq.350 g/mol, preferably Mw.gtoreq.380 g/mol, more preferably Mw.gtoreq.400 g/mol, still more preferably Mw.gtoreq.450 g/mol.

Furthermore, it is preferred that the group G ₁ A group selected from the group consisting of:

wherein:

x represents C-R, identical or different at each occurrence ^X Or N; provided that when X is the same as the group Ant ₁ X represents C when bonded;

E ¹ 、E ² 、E ³ 、E ⁴ represents, identically or differently, at each occurrence, a single bond, -BR ⁰ -、-C(R ⁰ ) ₂ -、-Si(R ⁰ ) ₂ -、-C(＝O)-、-O-、-S-、-S(＝O)-、-SO ₂ -、-N(R ⁰ ) -or-P (R) ⁰ ) -; provided that the radical E ¹ And E is ³ Only one of which may be a single bond and a group E ⁴ And E is ² Only one of which may be a single bond;

E ⁵ representative-BR ⁰ -、-C(R ⁰ ) ₂ -、-Si(R ⁰ ) ₂ -、-C(＝O)-、-O-、-S-、-S(＝O)-、-SO ₂ -、-N(R ⁰ ) -or-P (R) ⁰ ) -, preferably represents-C (R ⁰ ) ₂ -, -O-or-S-, more preferably represents-O-or-S-;

R ⁰ identically or differently on each occurrence represents: h, D, F, CN, a linear alkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10C atoms or a branched or cyclic alkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10C atoms, each of which may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, still more preferably 6 to 18 aromatic ring atoms, which may in each case be substituted by one or more groups R, where two adjacent substituents R ⁰ An aliphatic or aromatic ring system, which may be mono-or polycyclic, which may be substituted by one or more radicals R;

R ^X r has the same meaning as described above.

Preferably E ¹ 、E ² 、E ³ 、E ⁴ The same or different at each occurrence represents a single bond, -O-or-S-; provided that the radical E ¹ And E is ³ One of which is a single bond and the other is-O-or-S-, and the radical E ⁴ And E is ² One of which is a single bond and the other of which is-O-or-S-. More preferably E ¹ And E is ² represents-O-or-S-and E ³ And E is ⁴ Representing a single bond.

Among the structures of the formulae (G1-1) to (G1-12), the following structure is preferable: (G1-1), (G1-3), (G1-4), (G1-5), (G1-7), (G1-9), (G1-10), (G1-11) and (G1-12). The following structure is particularly preferred: (G1-1), (G1-3), (G1-4), (G1-5), (G1-9) and (G1-10).

Preferably, the compound of formula (H1) is selected from the compounds of the formula:

wherein the symbols have the same meaning as described above and wherein the compounds of formulae (G1-1-1) to (G1-12-3) contain at least one deuterium atom.

The host material (H1) is preferably a compound selected from the group consisting of compounds of the formulae (G1-1-1), (G1-2-1), (G1-3-1), (G1-4-2), (G1-5-1), (G1-6-1), (G1-7-1), (G1-8-1), (G1-9-3), (G1-10-1), (G1-10-3), (G1-11-1), (G1-11-3), (G1-12-1) and (G1-12-3). The host material (H1) is very preferably selected from the group consisting of compounds of the formulae (G1-1-1), (G1-3-1), (G1-4-2), (G1-5-1), (G1-7-1), (G1-9-1), (G1-10-1), (G1-11-1) and (G1-12-1).

According to a preferred embodiment, the label m in formula (H1) is equal to 0 and the first host compound of formula (H1) comprises only one group Ant ₁ 。

The bonding positions on the groups (G1-1) to (G1-10) may be numbered as follows:

the group Ant ₁ Examples of suitable bonding positions of (a) are shown in the following table:

the symbol "-" indicates the absence of the second group Ant ₁ . In the formulae (G1-1-1) to (G1-12-6), the compounds (G1-1-1), (G1-1-2), (G1-1-4), (G1-2-3), (G1-2-4), (G1-2-7), (G1-3-1), (G1-3-3), (G1-4-2), (G1-4-3), (G1-4-4), (G1-4-12), (G1-4-13), (G1-5-2), (G1-5-3), (G1-5-4), (G1-5-14), (G1-5-12), (G1-5-17), (G1-6-1), (G1-7-3), (G1-7-5), (G1-8-1), (G1-8-2), (G1-8-3), (G1-8-7), (G1-8-9), (G1-9) and (G1-8-9), (G1-9-3), (G1-9-5), (G1-10-1), (G1-10-3), (G1-10-7), (G1-11-2), (G1-11-6), (G1-11-5) and (G1-12-1) are preferred, wherein the second group Ant is absent ₁ The compounds of (C) and (G1-4-12) are more preferable. The following groups are highly preferred: (G1-1-1), (G1-1-2), (G1-2-3), (G1-2-4), (G1-3-1), (G1-4-2), (G1-4-3), (G1-4-4), (G1-5-2), (G1-5-3), (G1-5-4), (G1-7-1), (G1-7-2), (G1-8-1), (G1-8-2), (G1-8-3), (G1-9-1), (G1-10-1) and (G1-12-1).

Preferably, the group Ar ^A1 And Ar is a group ^B1 Selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorene, spirobifluorene, naphthalene, anthracene, phenanthrene, triphenylene, fluoranthene, naphthacene, chicory, benzanthracene, benzophenanthrene, pyrene or perylene, dibenzofuran, carbazole and dibenzothiophene, each of which may be substituted in any free position by one or more radicals R; and wherein Ar is ^A1 、Ar ^B1 Combinations of two or more of the foregoing groups are also possible. More preferably, the group Ar ^A1 And Ar is a group ^B1 And are selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl, tetraphenyl, naphthalene, phenanthrene, each of which may be substituted in any free position by one or more radicals R.

Preferably, the group Ant ₁ Is a group of the formulae (A1-1) to (A1-5):

the dotted bond in the formulae (A1-1) to (A1-5) represents a group G ₁ In which the group Ant is ₁ Can be bonded to the group G at any free position ₁ The method comprises the steps of carrying out a first treatment on the surface of the And wherein

R ^A9 To R ^A21 Represents, identically or differently on each occurrence, a group selected from: h, D, F, cl, br, I, CHO, CN, C (=O) Ar, P (=O) (Ar) ₂ ，S(＝O)Ar，S(＝O) ₂ Ar，N(R) ₂ ，N(Ar) ₂ ，NO ₂ ，Si(R) ₃ ，B(OR) ₂ ，OSO ₂ R, a linear alkyl, alkoxy or thioalkyl radical having from 1 to 40C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40C atoms, which may each be substituted by one or more radicals R, where in each case one or more non-adjacent CH ₂ The radicals may be substituted by RC=CR, C≡ C, si (R) ₂ 、Ge(R) ₂ 、Sn(R) ₂ 、C＝O、C＝S、C＝Se、P(＝O)(R)、SO、SO ₂ O, S or CONR and wherein one or more H atoms may be replaced by D, F, cl, br, I, CN or NO ₂ Alternatively, an aromatic ring or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which in each case may be substituted by one or more radicals R, and an aryloxy group having from 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R; wherein R is ^A9 To R ^A21 May together form an aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more groups R.

Preferably, R ^A1 To R ^A8 Identically or differently on each occurrence represents: h, D, F, straight-chain alkyl, alkoxy or thioalkyl having from 1 to 40, preferably from 1 to 20, more preferably from 1 to 10, C atomsGroups or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40, preferably 3 to 20, more preferably 3 to 10C atoms, each of which may be substituted by one or more groups R, where in each case one or more non-adjacent CH ₂ The radicals may be replaced by rc=cr, c≡ C, O or S and one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, particularly preferably 5 to 18, aromatic ring atoms, which in each case may be substituted by one or more radicals R. More preferably, R ^A1 To R ^A8 Identically or differently on each occurrence represents: h, D, F, a linear alkyl group having from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6C atoms or a branched or cyclic alkyl group having from 3 to 20, preferably from 3 to 10, more preferably from 3 to 6C atoms, each of which may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 30, more preferably from 5 to 18, aromatic ring atoms, which may in each case be substituted by one or more groups R. Particularly preferably, R ^A1 To R ^A8 Selected from H and D.

Preferably, R ^A9 To R ^A21 Identically or differently on each occurrence represents: h, D, F, a linear alkyl, alkoxy or thioalkyl group having from 1 to 40, preferably from 1 to 20, more preferably from 1 to 10, C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having from 3 to 40, preferably from 3 to 20, more preferably from 3 to 10, C atoms, which may each be substituted by one or more radicals R, where in each case one or more non-adjacent CH ₂ The radicals may be replaced by rc=cr, c≡ C, O or S and one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, particularly preferably 5 to 18, aromatic ring atoms, which in each case may be substituted by one or more radicals R. More preferably, R ^A9 To R ^A21 Identically or differently on each occurrence represents: h, D, F, straight-chain alkyl groups having 1 to 20, preferably 1 to 10, more preferably 1 to 6C atomsA group or a branched or cyclic alkyl group having 3 to 20, preferably 3 to 10, more preferably 3 to 6C atoms, each of which may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30, more preferably 5 to 18 aromatic ring atoms, which may in each case be substituted by one or more groups R. Particularly preferably, R ^A9 To R ^A21 Selected from H and D.

More preferably, the group Ant ₁ Is a group of the formulae (A1-1-D) to (A1-5-D):

wherein the method comprises the steps of

x is an integer from 0 to 8, more preferably from 1 to 8;

y1 is an integer from 0 to 5, more preferably from 1 to 5;

y2 is an integer from 0 to 4, more preferably from 1 to 4;

y3 is an integer from 0 to 3, more preferably from 1 to 3;

z is an integer from 0 to 7, more preferably from 1 to 7.

For example, if the label x represents 8, the anthracene group in formula (A1-1-D) contains 8 deuterium atoms, meaning that the anthracene group in formula (A1-1-D) is fully deuterated.

As described above, the compound of formula (H1) comprises at least one deuterium atom. The at least one deuterium atom can be a group Ant ₁ Or G ₁ Substituents on the same.

According to a preferred embodiment, said at least one deuterium atom is a group Ant ₁ Substituents on the same.

When at least one deuterium atom is a group Ant ₁ When the substituents are the above, preferred are:

-in formula (A1): at least one group R ^A1 To R ^A8 Represents deuterium atoms or groups Ar ^A1 At least one group R of (a) represents a deuterium atom;

-in formulae (A1-1) to (A1-5): at least one group R ^A1 To R ^A8 Represents a deuterium atom or at least one group R ^A9 To R ^A21 Represents a deuterium atom;

-in formulae (A1-1-D) to (A1-5-D): at least one of the labels selected from x, y1, y2, y3 and z present in the formula is not equal to 0.

According to a preferred embodiment, said at least one deuterium atom is a group G ₁ Substituents on the same.

In this case, at least one radical R is preferred ^X Represents a deuterium atom. More particularly, it is preferably present in the group G ₁ Substituent R in (a) ^X Represents at least 10% of deuterium atoms. More preferably, it is present in the group G ₁ Substituent R in (a) ^X Represents deuterium atoms, or is present in the group G ₁ Substituent R in (a) ^X Represents deuterium atoms, or is present in the group G ₁ Substituent R in (a) ^X Represents deuterium atoms, or is present in the group G ₁ Substituent R in (a) ^X Represents deuterium atoms, or is present in the group G ₁ Substituent R in (a) ^X Represents deuterium atoms, or is present in the group G ₁ Substituent R in (a) ^X Represents deuterium atoms, or is present in the group G ₁ Substituent R in (a) ^X Represents deuterium atoms, or is present in the group G ₁ Substituent R in (a) ^X Represents at least 90% of deuterium atoms.

Preferably, R ^X Identically or differently on each occurrence represents: h, D, F, a linear alkyl, alkoxy or thioalkyl group having from 1 to 40, preferably from 1 to 20, more preferably from 1 to 10, C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having from 3 to 40, preferably from 3 to 20, more preferably from 3 to 10, C atoms, which may each be substituted by one or more radicals R, where in each case one or more non-adjacent CH ₂ The radicals may be replaced by rc=cr, c≡ C, O or S and in which one or more H atoms may be presentTo be replaced by D or F, aromatic or heteroaromatic ring systems having from 5 to 60, preferably from 5 to 40, more preferably from 5 to 30, particularly preferably from 5 to 18, aromatic ring atoms, which may in each case be substituted by one or more radicals R. More preferably, R ^X Identically or differently on each occurrence represents: h, D, F, a linear alkyl group having from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6C atoms or a branched or cyclic alkyl group having from 3 to 20, preferably from 3 to 10, more preferably from 3 to 6C atoms, each of which may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 30, more preferably from 5 to 18, aromatic ring atoms, which may in each case be substituted by one or more groups R. More preferably, R ^X Selected from H and D.

It is particularly preferred that the compound of formula (H1) is at least 10% deuterated by a deuterium atom, wherein said deuterium atom is a group G ₁ Group Ant ₁ Or a group G ₁ And Ant ₁ Substituents on the same. This means that at least 10% of the available hydrogen atoms in the compound of formula (H1) are replaced by deuterium atoms. More preferably, the compound of formula (H1) is at least 20% deuterated, or at least 30% deuterated, or at least 40% deuterated, or at least 50% deuterated, or at least 60% deuterated, or at least 70% deuterated, or at least 80% deuterated, or at least 90% deuterated.

Examples of highly preferred compounds of formula (H1) are shown in the following table:

in structure, the term "D8" or "D4" means, for example, that the corresponding ring is substituted with 8, 4 deuterium atoms, respectively.

Preferably, the group G ₂ A group selected from the group consisting of:

wherein:

y represents C-R identically or differently on each occurrence ^Y Or N; provided that when Y is the same as the group Ant ₂ Y represents C when bonded; and wherein the symbol R ^Y Has the same meaning as described above; and is also provided with

R ^B0 Has the same meaning as described above.

Preferably, R ^B0 Identically or differently on each occurrence represents: h, a linear alkyl group having from 1 to 40, preferably from 1 to 20, more preferably from 1 to 10C atoms or a branched or cyclic alkyl group having from 3 to 40, preferably from 3 to 20, more preferably from 3 to 10C atoms, each of which may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 20, more preferably from 6 to 18, aromatic ring atoms, which may in each case be substituted by one or more groups R; wherein two adjacent substituents R ^B0 A mono-or polycyclic aliphatic or aromatic ring system may be formed, which may be substituted with one or more groups R.

Among the groups (G2-1) to (G2-5), the groups (G2-1) and (G2-2) are preferable.

Preferably, the compound of formula (H2) is selected from the group of the following formulae:

wherein the symbols have the same meaning as described above.

Among the compounds of the formulae (G2-1-1) to (G2-5-2), the following compounds are preferred: (G2-1-1), (G2-2-1), (G2-4-1), (G2-5-1), and (G2-5-2), more preferably (G2-1-1), (G2-2-1), (G2-5-1), and very preferably (G2-1-1), (G2-2-1).

The bonding positions on the groups (G2-1) to (G2-5) may be numbered as follows:

the group Ant ₂ The preferred bonding positions of (a) are shown in the following table:

among the compounds of the formulae (G2-1-1) to (G2-5-20), the following compounds are preferred: (G2-1-6), (G2-1-7), (G2-1-9), (G2-1-10), (G2-1-11), (G2-1-12), (G2-2-7), (G2-2-8), (G2-2-9), (G2-2-10), (G2-3-7), (G2-3-8), (G2-3-9), (G2-4-5), (G2-4-7), (G2-5-5), (G2-5-7), (G2-5-15), (G2-5-17) and (G2-5-20). More preferred are compounds of the formula: (G2-1-6), (G2-1-9), (G2-2-8), (G2-2-9), (G2-4-7), (G2-5-15) and (G2-5-20).

Preferably, R ^Y The same or different representatives at each occurrence: h, F, a linear alkyl, alkoxy or thioalkyl radical having from 1 to 40, preferably from 1 to 20, more preferably from 1 to 10, C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40, preferably from 3 to 20, more preferably from 3 to 10, C atoms, which may each be substituted by one or more radicals R, where in each case one or more non-adjacent CH ₂ The radicals may be replaced by rc=cr, c≡ C, O or S and one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, particularly preferably 5 to 18, aromatic ring atoms, which in each case may be substituted by one or more radicals R. More preferably, R ^Y The same or different representatives at each occurrence: h, F, a linear alkyl group having from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6C atoms or a branched or cyclic alkyl group having from 3 to 20, preferably from 3 to 10, more preferably from 3 to 6C atoms, each of which may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 30, more preferably from 5 to 18, aromatic ring atoms, which may in each case be substituted by one or more groups R. More preferably, R ^Y Represents H.

The group Ant ₂ Preferably a group of the formulae (A2-1) to (A2-5):

wherein the dotted bond in formulae (A2-1) to (A2-5) represents a group G ₂ In which the group Ant is ₂ Can be arbitrarily fromFrom the position and G ₂ Bonding; and wherein

R ^B9 To R ^B21 Represents, identically or differently on each occurrence, a group selected from: h, F, cl, br, I, CHO, CN, C (=O) Ar, P (=O) (Ar) ₂ ，S(＝O)Ar，S(＝O) ₂ Ar，N(R) ₂ ，N(Ar) ₂ ，NO ₂ ，Si(R) ₃ ，B(OR) ₂ ，OSO ₂ R, a linear alkyl, alkoxy or thioalkyl radical having from 1 to 40C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40C atoms, which may each be substituted by one or more radicals R, where in each case one or more non-adjacent CH ₂ The radicals may be substituted by RC=CR, C≡ C, si (R) ₂ 、Ge(R) ₂ 、Sn(R) ₂ 、C＝O、C＝S、C＝Se、P(＝O)(R)、SO、SO ₂ O, S or CONR and wherein one or more H atoms may be replaced by F, cl, br, I, CN or NO ₂ Alternatively, an aromatic ring or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which in each case may be substituted by one or more radicals R, and an aryloxy group having from 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R; wherein R is ^B9 To R ^B21 May together form an aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more groups R.

Preferably, R ^B1 To R ^B8 Identically or differently on each occurrence represents: h, F, a linear alkyl, alkoxy or thioalkyl group having from 1 to 40, preferably from 1 to 20, more preferably from 1 to 10, C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having from 3 to 40, preferably from 3 to 20, more preferably from 3 to 10, C atoms, which may each be substituted by one or more radicals R, an aromatic or heteroaromatic ring system having from 5 to 60, preferably from 5 to 40, more preferably from 5 to 30, particularly preferably from 5 to 18, aromatic ring atoms, which may in each case be substituted by one or more radicals R. More preferably, R ^B1 To R ^B8 The same or different representatives at each occurrence: h, F, having 1 to 20, preferably1 to 10, more preferably 1 to 6, C atoms or branched or cyclic alkyl groups having 3 to 20, preferably 3 to 10, more preferably 3 to 6, C atoms, each of which may be substituted by one or more groups R, aromatic or heteroaromatic ring systems having 5 to 40, preferably 5 to 30, more preferably 5 to 18, aromatic ring atoms, which may in each case be substituted by one or more groups R. Particularly preferably, R ^B1 To R ^B8 Represents H.

Preferably, R ^B9 To R ^B21 Identically or differently on each occurrence represents: h, F, a linear alkyl, alkoxy or thioalkyl group having from 1 to 40, preferably from 1 to 20, more preferably from 1 to 10, C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having from 3 to 40, preferably from 3 to 20, more preferably from 3 to 10, C atoms, which may each be substituted by one or more radicals R, an aromatic or heteroaromatic ring system having from 5 to 60, preferably from 5 to 40, more preferably from 5 to 30, particularly preferably from 5 to 18, aromatic ring atoms, which may in each case be substituted by one or more radicals R. More preferably, R ^B9 To R ^B21 Identically or differently on each occurrence represents: h, F, a linear alkyl group having from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6C atoms or a branched or cyclic alkyl group having from 3 to 20, preferably from 3 to 10, more preferably from 3 to 6C atoms, each of which may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 30, more preferably from 5 to 18, aromatic ring atoms, which may in each case be substituted by one or more groups R.

Examples of highly preferred compounds of formula (H2) are shown in the following table:

preferably, the group AR ^AS And AR ^BS And represents, identically or differently on each occurrence, phenyl, biphenyl, fluorene, spirobifluorene, naphthalene, phenanthrene, anthracene, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, benzopyridine, benzopyridazine, benzopyrimidine and quinazoline, each of which may be substituted by one or more groups R. More preferably, the group AR ^AS And AR ^BS The same or different at each occurrence represent phenyl, biphenyl or naphthalene, each of which may be substituted by one or more radicals R.

Preferably, R, identically or differently at each occurrence, represents the representation: h, D, F, CN, N (Ar) ₂ A linear alkyl, alkoxy or thioalkyl radical having from 1 to 40, preferably from 1 to 20, more preferably from 1 to 10, C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40, preferably from 3 to 20, more preferably from 3 to 10, C atoms, which may each be substituted by one or more radicals R', where in each case one or more non-adjacent CH ₂ The radicals may be replaced by R ' c=cr ', c≡ C, O or S, and one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, particularly preferably 6 to 18, aromatic ring atoms, which in each case may be substituted by one or more radicals R '.

Preferably, ar is identical or different on each occurrence an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 30, more preferably from 5 to 25, very preferably from 6 to 18, aromatic ring atoms, which in each case may also be substituted by one or more radicals R';

preferably, R', identically or differently at each occurrence, represents: h, D, F, cl, br, I, CN, a linear alkyl group having 1 to 10C atoms or a branched or cyclic alkyl group having 3 to 10C atoms, wherein in each case one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 18C atoms.

According to the invention, the composition comprises a first host material of formula (H1), a second host material of formula (H2), and a dopant material. The dopant material is preferably a fluorescent emitter.

Preferably, the composition comprises at least one fluorescent emitter comprising at least one of the following groups:

-an arylamine containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to nitrogen;

-bridged triarylamines;

-a fused aromatic or heteroaromatic ring system having at least 14 aromatic ring atoms;

-indenofluorene, indenofluorene amine or indenofluorene diamine;

-benzindene fluorene, benzindene fluorene amine or benzindene fluorene diamine;

-dibenzoindenofluorene, dibenzoindenofluorene amine or dibenzoindenofluorene diamine;

indenofluorenes containing fused aryl groups having at least 10 aromatic ring atoms;

-bis-indenoindenofluorene;

-indenofluor, indenofluorene amine or indenofluorene diamine;

-fluorene dimers;

-a phenoneAn oxazine; or (b)

-boron derivatives.

More preferably, the composition comprises at least one fluorescent emitter of the following formula (E-1), (E-2), (E-3) or (E-4):

wherein the method comprises the steps of

Ar ¹⁰ 、Ar ¹¹ 、AR ¹² Identically or differently on each occurrence are aromatic or heteroaromatic ring systems having from 6 to 60 aromatic ring atoms, which may also be substituted in each case by one or more radicals R; provided that at least one group Ar ¹⁰ 、Ar ¹¹ 、Ar ¹² Is an aromatic or heteroaromatic ring system having from 10 to 40 aromatic ring atoms, comprising at least one fused aryl or heteroaryl group consisting of 2 to 4 aromatic rings fused to each other, wherein the aromatic or heteroaromatic ring system may be substituted with one or more groups R;

r has the same definition as above; and is also provided with

e is 1, 2, 3 or 4; more preferably, e is 1;

wherein the method comprises the steps of

Ar ²⁰ 、Ar ²¹ 、Ar ²² An aryl or heteroaryl group having 6 to 30 aromatic ring atoms, which may in each case also be substituted by one or more radicals R, is identical or different on each occurrence;

E ²⁰ is selected from BR, C (R ⁰ ) ₂ 、Si(R ⁰ ) ₂ 、C＝O、C＝NR ⁰ 、C＝C(R ⁰ ) ₂ 、O、S、S＝O、SO ₂ 、NR ⁰ 、PR ⁰ 、P(＝O)R ⁰ Or P (=S) R ⁰ The group in (a); wherein Ar is ²⁰ 、Ar ²¹ And E is ²⁰ Together form a five-membered or six-membered ring, and Ar ²¹ 、Ar ²³ And E is ²⁰ Together forming a five-membered or six-membered ring;

R ⁰ identically or differently on each occurrence represents: h, D, F, a linear alkyl radical having from 1 to 20, preferably from 1 to 10, C atoms or a linear alkyl radical having from 3 to 20, preferably from 3 toBranched or cyclic alkyl radicals of 10C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH' s ₂ The radicals may be replaced by O or S and one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 30, more preferably from 6 to 18, aromatic ring atoms, which in each case may be substituted by one or more radicals R, two adjacent radicals R ⁰ May together form an aliphatic or aromatic ring system which may be substituted by one or more groups R,

r has the same definition as above;

p, q are, identically or differently, at each occurrence, 0 or 1, provided that p+q=1;

r is 1, 2 or 3;

wherein the method comprises the steps of

Ar ³⁰ 、Ar ³¹ 、Ar ³² Represents identically or differently on each occurrence a substituted or unsubstituted aryl or heteroaryl group having from 5 to 22, preferably from 5 to 18, more preferably from 6 to 14, aromatic ring atoms;

E ³⁰ represents B or N;

E ³¹ 、E ³² 、E ³³ represents O, S, C (R ⁰ ) ₂ 、C＝O、C＝S、C＝NR ⁰ 、C＝C(R ⁰ ) ₂ 、Si(R ⁰ ) ₂ 、BR ⁰ 、NR ⁰ 、PR ⁰ 、SO ₂ 、SeO ₂ Or a chemical bond, provided that if E ³⁰ B is a group E ³¹ 、E ³² 、E ³³ At least one of them represents NR ⁰ And if E ³⁰ Is N, then the radical E ³¹ 、E ³² 、E ³³ At least one of them represents BR ⁰ ；

R ⁰ Having the same definition as above;

s, t, u are, identically or differently, at each occurrence, 0 or 1, provided that s+t+u.gtoreq.1;

wherein the method comprises the steps of

Ar ⁴⁰ 、Ar ⁴¹ 、Ar ⁴² Represents identically or differently on each occurrence a substituted or unsubstituted aryl or heteroaryl group having from 5 to 22, preferably from 5 to 18, more preferably from 6 to 14, aromatic ring atoms;

E ⁴¹ 、E ⁴² 、E ⁴³ represents O, S, C (R ⁰ ) ₂ 、C＝O、C＝S、C＝NR ⁰ 、C＝C(R ⁰ ) ₂ 、Si(R ⁰ ) ₂ 、BR ⁰ 、NR ⁰ 、PR ⁰ 、SO ₂ 、SeO ₂ Or a bond, provided that the radical E ⁴¹ 、E ⁴² 、E ⁴³ Is present and represents a chemical bond;

R ⁰ having the same definition as above;

i. g, h are, identically or differently, at each occurrence, 0 or 1, provided that i+g+h.gtoreq.1.

Preferably, the fluorescent emitter of formula (E-1) comprises at least one group Ar ¹⁰ 、Ar ¹¹ Or Ar ¹² Preferably Ar ¹⁰ Selected from the group consisting of formula (Ar) ¹⁰ -1) to (Ar) ¹⁰ -24) groups:

wherein the radical Ar ¹⁰ -1 to Ar ¹⁰ -24 may be substituted in all free positions by one or more groups R; and wherein

E ¹⁰ Is selected from BR, identically or differently at each occurrence ⁰ 、C(R ⁰ ) ₂ 、Si(R ⁰ ) ₂ 、C＝O、C＝NR ⁰ 、C＝C(R ⁰ ) ₂ 、O、S、S＝O、SO ₂ 、NR ⁰ 、PR ⁰ 、P(＝O)R ⁰ Or P (=S) R ⁰ In (a) is preferably a group E ¹⁰ Is C (R) ⁰ ) ₂ ；

Wherein R is ⁰ Having the same definition as above;

E ¹¹ is selected identically or differently at each occurrence from c= O, O, S, S =o or SO ₂ Preferably O or S, more preferably O; and is also provided with

Ar ¹³ Identically or differently on each occurrence are aromatic or heteroaromatic ring systems having from 5 to 60 aromatic ring atoms, which may also be substituted in each case by one or more radicals R.

According to a preferred embodiment, the luminophore of formula (E-1) comprises a compound selected from the group consisting of compounds of formula (Ar) ¹⁰ -15) to (Ar) ¹⁰ Group Ar in the group of-22) ¹⁰ Wherein d is preferably equal to 1 and wherein preferably at least one group Ar ¹¹ 、Ar ¹² Selected from the formula (Ar) ¹⁰ -15) to (Ar) ¹⁰ -22) a group.

According to a very preferred embodiment, the luminophores according to formula (E-1) are selected from luminophores according to formulae (E-1-1) to (E-1-6),

Wherein the symbols have the same meaning as described above, and wherein:

f is 0, 1 or 2; and is also provided with

The above benzene ring in the compounds of the formulae (E-1-1) to (E-1-6) may be substituted in all free positions by one or more radicals R.

Particularly preferably, the compounds of the formula (E-1) are selected from the compounds of the formulae (E-1-1-A) to (E-1-6-A),

wherein the symbols and labels have the same meaning as described above, and wherein the above-mentioned benzene rings in the compounds of the formulae (E-1-1-A) to (E-1-6-A) may be substituted at all free positions by one or more groups R.

Preferably, the fluorescent light-emitting body of formula (E-2) is selected from the fluorescent light-emitting bodies of formulae (E-2-1) to (E-2-43),

wherein the groups of formulae (E-2-1) to (E-2-43) may be substituted at all free positions by one or more radicals R; wherein E is ²⁰ Has the same definition as described above. Preferably E ²⁰ Is C (R) ⁰ ) ₂ 。

The compound of formula (E-2) is preferably selected from the compounds of formulae (E-2-32) to (E-2-43). More preferably, the compound of formula (E-2) is selected from the group consisting of compounds (E-2-32-A) to (E-2-43-A):

wherein the symbols have the same meanings as described above, and wherein the above-mentioned benzene rings and naphthalene rings in the compounds of the formulae (E-2-32-A) to (E-2-43-A) may be substituted at all free positions by one or more groups R.

Preferably, the fluorescent light-emitting body of formula (E-3) is selected from fluorescent light-emitting bodies of formula (E-3-1),

wherein the symbols and marks have the same meaning as described above.

More preferably, the fluorescent light-emitting body of formula (E-3) is selected from fluorescent light-emitting bodies of formula (E-3-2),

wherein symbol E ³⁰ To E to ³³ Has the same meaning as described above; wherein t is 0 or 1, wherein when t is 0, no group E is present ³² And there is a group R ¹⁰ Its substitution is with E ³² A linked bond; and wherein

R ¹⁰ Identically or differently on each occurrence represents: h, D, F, cl, br, I, CHO, CN, C (=O) Ar, P (=O) (Ar) ₂ ，S(＝O)Ar，S(＝O) ₂ Ar，N(R′) ₂ ，N(Ar) ₂ ，NO ₂ ，Si(R′) ₃ ，B(OR′) ₂ ，OSO ₂ R 'is a linear alkyl, alkoxy or thioalkyl radical having from 1 to 40C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40C atoms, which may each be substituted by one or more radicals R', where in each case one or more non-adjacent CH ₂ The radicals may be substituted by R ' C=CR ', C≡ C, si (R ') ₂ 、Ge(R′) ₂ 、Sn(R′) ₂ 、C＝O、C＝S、C＝Se、P(＝O)(R′)、SO、SO ₂ O, S or CONR' and wherein one or more H atoms may be replaced by D, F, cl, br, I, CN or NO ₂ Alternatively, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which in each case may be substituted by one or more radicals R ', or an aryloxy group having from 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R'; wherein two adjacent substituents R ¹⁰ May together form an aliphatic or aromatic ring system, which may be substituted by one or more groups R'; wherein R' has the same definition as above.

Still more preferably, the fluorescent light-emitting body of formula (E-3) is selected from the fluorescent light-emitting bodies of formulae (E-3-3) and (E-3-4),

wherein the symbols and marks have the same meaning as described above.

Preferably, the fluorescent light-emitting body of formula (E-4) is selected from fluorescent light-emitting bodies of formula (E-4-1) or (E-4-2),

wherein the method comprises the steps of

E ⁴¹ And E is ⁴² Represents O, S, C (R ⁰ ) ₂ 、C＝O、C＝S、C＝NR ⁰ 、C＝C(R ⁰ ) ₂ 、Si(R ⁰ ) ₂ 、BR ⁰ 、NR ⁰ 、PR ⁰ 、SO ₂ 、SeO ₂ Or a chemical bond, wherein E ⁴¹ Preferably a bond;

R ²⁰ identically or differently on each occurrence represents: h, D, F, cl, br, I, CHO, CN, C (=O) Ar, P (=O) (Ar) ₂ ，S(＝O)Ar，S(＝O) ₂ Ar，N(R′) ₂ ，N(Ar) ₂ ，NO ₂ ，Si(R′) ₃ ，B(OR′) ₂ ，OSO ₂ R 'is a linear alkyl, alkoxy or thioalkyl radical having from 1 to 40C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40C atoms, which may each be substituted by one or more radicals R', where in each case one or more non-adjacent CH ₂ The radicals may be substituted by R ' C=CR ', C≡ C, si (R ') ₂ 、Ge(R′) ₂ 、Sn(R′) ₂ 、C＝O、C＝S、C＝Se、P(＝O)(R′)、SO、SO ₂ O, S or CONR' and wherein one or more H atoms may be replaced by D, F, cl, br, I, CN or NO ₂ Alternatively, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which in each case may be substituted by one or more radicals R ', or an aryloxy group having from 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R'; wherein two adjacent substituents R ²⁰ Can together form an aliphatic or aromatic ring system, which can be substituted with oneOne or more groups R' are substituted; wherein R' has the same definition as above;

g is 0 or 1.

More preferably, the fluorescent light-emitting body of formula (E-4) is selected from fluorescent light-emitting bodies of formula (E-4-1-A) or (E-4-2-A),

wherein the symbols have the same meaning as described above.

According to a preferred embodiment, the fluorescent emitter of formula (E-1), (E-2), (E-3) or (E-4) comprises a group RS, wherein the group RS is selected from the group consisting of:

branched or cyclic alkyl groups represented by the following groups of the formula (RS-a),

wherein the method comprises the steps of

R ²² 、R ²³ 、R ²⁴ And is selected, identically or differently, at each occurrence, from: h, a linear alkyl radical having from 1 to 10 carbon atoms or a branched or cyclic alkyl radical having from 3 to 10 carbon atoms, where the radicals mentioned can each be replaced by one or more radicals R ²⁵ Substituted, and wherein the radicals R ²² 、R ²³ 、R ²⁴ Two or all of the radicals R ²² 、R ²³ 、R ²⁴ Can be linked to form a group which can be substituted with one or more radicals R ²⁵ A substituted (poly) cyclic alkyl group;

R ²⁵ is selected identically or differently on each occurrence from a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms;

provided that at each occurrence there is a base R ²² 、R ²³ And R is ²⁴ At least one of (a) is other than H, provided that at each occurrence all groups R ²² 、R ²³ And R is ²⁴ Together having at least 4 carbon atomsWith the proviso that at each occurrence, if the radicals R ²² 、R ²³ 、R ²⁴ Two of which are H, the remaining groups are not linear; or alternatively

-branched or cyclic alkoxy groups represented by the following formula (RS-b)

Wherein the method comprises the steps of

R ²⁶ 、R ²⁷ 、R ²⁸ And is selected, identically or differently, at each occurrence, from: h, a linear alkyl radical having from 1 to 10 carbon atoms or a branched or cyclic alkyl radical having from 3 to 10 carbon atoms, where the radicals mentioned may each be defined as one or more radicals R ²⁵ Substituted, and wherein the radicals R ²⁶ 、R ²⁷ 、R ²⁸ Two or all of the radicals R ²⁶ 、R ²⁷ 、R ²⁸ May be linked to form one or more groups R which may be as defined above ²⁵ A substituted (poly) cyclic alkyl group;

provided that at each occurrence the radicals R ²⁶ 、R ²⁷ And R is ²⁸ Only one of which may be H;

an aralkyl group represented by the following formula (RS-c)

Wherein the method comprises the steps of

R ²⁹ 、R ³⁰ 、R ³¹ And is selected, identically or differently, at each occurrence, from: h, a linear alkyl radical having from 1 to 10 carbon atoms or a branched or cyclic alkyl radical having from 3 to 10 carbon atoms, where the radicals mentioned can each be replaced by one or more radicals R ³² Substituted, or aromatic ring systems having 6 to 30 aromatic ring atoms, which in each case may be substituted by one or more radicals R ³² Substituted, and wherein the radicals R ²⁹ 、R ³⁰ 、R ³¹ Two or all of which may be linked to form groups each of which may be substituted with one or more groups R ³² A substituted (poly) cyclic alkyl group or an aromatic ring system;

R ³² and is selected, identically or differently, at each occurrence, from: a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms;

provided that at each occurrence there is a base R ²⁹ 、R ³⁰ And R is ³¹ At least one of which is not H and which is based on R at each occurrence ²⁹ 、R ³⁰ And R is ³¹ Is or comprises an aromatic ring system having at least 6 aromatic ring atoms;

an aromatic ring system represented by the following formula (RS-d)

Wherein the method comprises the steps of

R ⁴⁰ To R ⁴⁴ And is selected, identically or differently, at each occurrence, from: h, a linear alkyl radical having from 1 to 10 carbon atoms or a branched or cyclic alkyl radical having from 3 to 10 carbon atoms, where the radicals mentioned can each be replaced by one or more radicals R ³² Substituted, or aromatic ring systems having 6 to 30 aromatic ring atoms, which in each case may be substituted by one or more radicals R ³² Substituted, and wherein two or more of the radicals R ⁴⁰ To R ⁴⁴ Can be linked to form one or more radicals R each of which can be defined as above ³² A substituted (poly) cyclic alkyl group or an aromatic ring system; or alternatively

A group of formula (RS-e),

wherein the dotted bond in formula (RS-e) represents fluorescenceBonding of light emitters, wherein Ar ⁵⁰ 、Ar ⁵¹ Represents, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R; and wherein m is an integer selected from 1 to 10.

Preferably, the label m in the group of formula (RS-e) is an integer selected from 1 to 6, very preferably from 1 to 4.

Preferably Ar ⁵⁰ 、Ar ⁵¹ Represents, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 30, more preferably from 6 to 18, aromatic ring atoms, which may in each case be substituted by one or more radicals R. More preferably Ar ⁵⁰ 、Ar ⁵¹ Selected from phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorene, spirobifluorene, naphthalene, anthracene, phenanthrene, biphenylene, fluoranthene, dibenzofuran, carbazole and dibenzothiophene, which in each case may be substituted by one or more groups R. Very preferably, at least one group Ar ⁵⁰ Or Ar ⁵¹ Is fluorene, which may be substituted with one or more groups R.

More particularly, it is preferred that at least one group Ar ⁵⁰ Representing formula (Ar 50-2) and/or at least one group Ar ⁵¹ Represented by (Ar 51-2),

wherein the method comprises the steps of

The dotted bond in formula (Ar 50-2) represents a fluorescent emitter and a group Ar ⁵⁰ Or Ar ⁵¹ Is a bond of (2); and the dotted bond in formula (Ar 51-2) represents Ar ⁵⁰ Is a bond of (2);

E ⁴ selected from-C (R) ^0a ) ₂ -、-Si(R ^0a ) ₂ -, -O-, -S-or-N (R) ^0a ) -, preferably C (R ^0a ) ₂ ；

R ^0a Identically or differently on each occurrence represents: h, D, F, CN, having 1 to 40, preferably 1 to 20, more preferably 1 to 10A linear alkyl group of C atoms or a branched or cyclic alkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10C atoms, each of which may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms, which may in each case be substituted by one or more groups R; wherein two adjacent substituents R ^0a An aliphatic or aromatic ring system, which may be monocyclic or polycyclic, which may be substituted by one or more radicals R, has the same meaning as described above; and is also provided with

The groups of formulae (Ar 50-2) and (Ar 51-2) may be substituted at each free position with a group R having the same meaning as described above.

The group RS is preferably located at its substitution R, R ⁰ Or the position of R'.

Examples of fluorescent emitters which can be used in the composition comprising the compounds of formulae (H1) and (H2) are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chicory amines or aromatic chicory diamines. Aromatic anthraceneamines are understood to mean compounds in which one diarylamino group is directly bonded to the anthracene group, preferably in the 9-position. Aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are directly bonded to the anthracene groups, preferably in the 9,10 position. Aromatic pyrenamines, pyrenediamines, chicory amines and chicory diamines are defined in a similar manner thereto, with diarylamino groups bonded to pyrene preferably in the 1-or 1, 6-positions. Also preferred luminophores are bridged triarylamines, e.g. according to WO 2019/111971, WO 2019/240251 and WO 2020/067290. Also preferred luminophores are indenofluorene amine or indenofluorene diamine, e.g. according to WO 2006/108497 or WO 2006/122630, benzoindenofluorene amine or benzoindenofluorene diamine, e.g. according to WO 2008/006449, and dibenzoindenofluorene amine or dibenzoindenofluorene diamine, e.g. according to WO 2007/140847; and indenofluorene derivatives comprising a fused aryl group as disclosed in WO 2010/012328. Still further preferred luminophores are benzanthracene derivatives as disclosed in WO 2015/158409, anthracene derivatives as disclosed in WO 2017/036573, fluorenedi linked by a heteroaryl group as disclosed in WO 2016/150344 Polymers, or phenones as disclosed in WO 2017/028940 and WO 2017/028941An oxazine derivative. Also preferred are pyrene aryl amines disclosed in WO 2012/048780 and WO 2013/185871. Also preferred are benzoindenofluorene disclosed in WO 2014/037077, benzofluorenamine disclosed in WO 2014/106522, and indenofluorene disclosed in WO 2014/111269 or WO 2017/036574, WO 2018/007421. Also preferred are luminophores comprising dibenzofuran or indenodibenzofuran moieties as disclosed in WO 2018/095888, WO 2018/095940, WO 2019/076789, WO 2019/170572 and unpublished applications PCT/EP2019/072697, PCT/EP2019/072670 and PCT/EP 2019/072662. Preference is likewise given to boron derivatives as disclosed, for example, in WO 2015/102118, CN108409769, CN107266484, WO2017195669, US2018069182 and the unpublished applications EP 19168728.4, EP 19199326.0 and EP 19208643.7.

In the case of the present invention, very suitable fluorescent luminophores are indenofluorene derivatives disclosed in WO 2018/007421 and dibenzofuran derivatives disclosed in WO 2019/076789.

Examples of preferred fluorescent emissive compounds that can be used in compositions comprising compounds of formulas (H1) and (H2) are described in the following table:

According to the application, the compound of formula (H1) and the compound of formula (H2) are present together in a composition, preferably in a homogeneous mixture.

Preferably, the compound of formula (H1) is present in the composition in a proportion equal to or greater than 1% by weight of the composition. More preferably, the compound of formula (H1) is present in the composition in a proportion of from 1 to 99%, preferably from 10 to 95%, more preferably from 20 to 90%, particularly preferably from 30 to 85%, very particularly preferably from 40 to 80%.

Preferably, the compound of formula (H2) is present in the composition in a proportion equal to or greater than 1% by weight of the composition. More preferably, the compound of formula (H2) is present in the composition in a proportion of from 1 to 99%, preferably from 5 to 90%, more preferably from 10 to 80%, particularly preferably from 15 to 70%, very particularly preferably from 20 to 60%.

According to a preferred embodiment, the composition according to the application further comprises at least one fluorescent emitter. In this case, it is preferable that the fluorescent light-emitting body is present in the composition in a proportion of 0.1 to 50.0%, preferably 0.5 to 20.0%, particularly preferably 1.0 to 10.0%.

For the purposes of the present application, the proportion expressed in% is considered to mean% by volume if the compound is applied from the gas phase and% by weight if the compound is applied from the solution.

For the treatment of the compounds according to the invention from the liquid phase, for example by a coating method such as spin coating or by a printing method, formulations of the compositions according to the invention are required. These formulations can be, for example, solutions, dispersions or emulsions. A mixture of two or more solvents may be preferably used for this purpose. The solvent is preferably selected from organic and inorganic solvents, more preferably organic solvents. The solvent is very preferably selected from hydrocarbons, alcohols, esters, ethers, ketones and amines. Suitable and preferred solvents are, for example, toluene, anisole, o-, m-or p-xylene, methyl benzoate, mesitylene, tetrahydronaphthalene, veratrole, THF, methyl-THF, THP, chlorobenzene, di-Alkyl, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 1-ethylnaphthalene, decylbenzene, phenylnaphthalene, menthyl isovalerate, p-toluyl isobutyrate, cyclohexyl caproate, ethyl p-toluate, ethyl orthotoluate, ethyl meta-toluate, decalin, ethyl 2-methoxybenzoate, dibutylaniline, dicyclohexyl ketone, dimethyl isosorbide, decalin, 2-methylbiphenyl, ethyl octanoate, octyl octanoate, diethyl sebacate, 3-dimethylbiphenyl, 1, 4-dimethylnaphthalene, 2' -dimethylbiphenyl, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, benzol, butyl benzoate, cyclohexyl, decalin, Dodecylbenzene, ethyl benzoate, indane, NMP, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane or a mixture of these solvents.

The invention therefore also relates to a formulation comprising a compound of formula (H1) and a compound of formula (H2) according to the invention and at least one solvent. The solvent may be one of the solvents mentioned above or a mixture of these solvents.

The proportion of organic solvent in the formulation according to the invention is preferably at least 60% by weight, preferably at least 70% by weight and more preferably at least 80% by weight, based on the total weight of the formulation.

The formulations according to the invention can be used to produce layers or multilayer structures in which organic functional materials are present in the layers, as is required for the production of preferred electronic or optoelectronic components, such as OLEDs.

The formulation of the invention can preferably be used to form a functional layer comprising the composition according to the invention on a substrate or on one of the layers applied to a substrate.

Yet another object of the invention is a method of manufacturing an electronic device wherein at least one layer is obtained from the application of the formulation of the invention. Preferably, the formulation according to the invention is applied to a substrate or another layer and then dried.

The functional layer resulting from the formulation according to the invention can be manufactured by, for example, flow coating, dip coating, spray coating, spin coating, screen printing, relief printing, intaglio printing, rotary printing, roll coating, flexography, offset printing or nozzle printing, preferably ink jet printing on a substrate or on one of the layers applied to a substrate.

After the formulation according to the invention has been applied to a substrate or to a functional layer that has been applied, a drying step can be carried out to remove the solvent. Preferably, the drying step packageIncluding vacuum drying, which is preferably followed by annealing the layer. The vacuum drying can be preferably at 10 ^-7 In the range of mbar to 1bar, particularly preferably in the range of 10 ^-6 At a pressure in the range of mbar to 1 bar. The vacuum drying is preferably carried out at a temperature in the range of 10 to 40 ℃, more preferably in the range of 15 to 30 ℃. The vacuum drying step is preferably followed by a thermal annealing of the layer. The thermal annealing of the layer is preferably performed at a temperature of 120 ℃ to 180 ℃, preferably 130 ℃ to 170 ℃, more preferably 140 ℃ to 160 ℃.

The invention therefore relates to a method of manufacturing an electronic device comprising at least one layer comprising a composition according to the invention, wherein the method comprises the steps of:

a) Preparing a formulation according to the invention;

b) Applying the formulation prepared in step a) onto a substrate or another layer to form a layer comprising a composition according to the invention;

c) The layer was dried to remove the solvent.

Preferably, in step b), the formulation is applied by treatment from the liquid phase, more preferably by a coating method or a printing method, very preferably by a printing method, especially preferably by an inkjet printing method.

Another object of the invention is an electronic device comprising an anode, a cathode and at least one functional layer in between, wherein the functional layer comprises a composition according to the invention. Preferably, at least one functional layer comprising the composition according to the invention is a light emitting layer.

The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits, organic field effect transistors, organic thin film transistors, organic light emitting transistors, organic solar cells, dye sensitized organic solar cells, organic optical detectors, organic photoreceptors, organic field quench devices, light emitting electrochemical cells, organic laser diodes and organic plasma light emitting devices. More preferably, the electronic device is an organic electroluminescent device (OLED).

The organic electroluminescent device comprises a cathode, an anode and at least one light-emitting layer comprising the composition according to the invention. In addition to these layers, it may also contain other layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. It is also possible to introduce an intermediate layer between the two light-emitting layers, which has, for example, an exciton blocking function. However, it should be noted that each of these layers need not necessarily be present. Here, the organic electroluminescent device may include one light emitting layer or a plurality of light emitting layers. If a plurality of light-emitting layers are present, these preferably have a plurality of emission maxima in total between 380nm and 750nm, resulting in an overall white emission, i.e. various light-emitting compounds capable of fluorescing or phosphorescing are used in the light-emitting layers. Particularly preferred are systems with three light-emitting layers, wherein the three layers exhibit blue, green and orange or red light emission (see e.g. WO 2005/01013 for basic structures). These can be fluorescent or phosphorescent light-emitting layers or mixed systems in which fluorescent and phosphorescent light-emitting layers are bonded to one another.

Related electronic devices may comprise a single light emitting layer comprising a composition according to the invention, or it may comprise two or more light emitting layers.

The composition according to the invention may comprise one or more other matrix materials.

Preferred other matrix materials are selected from: an oligomeric arylene group (e.g. 2,2', 7' -tetraphenylspirobifluorene, or dinaphthyl anthracene according to EP 676861), in particular an oligomeric arylene group containing fused aromatic groups; an oligoarylene ethylene subunit (e.g., DPVBi or spiro-DPVBi according to EP 676861); a polypodal metal complex (e.g. according to WO 2004/081017); hole-conducting compounds (e.g. according to WO 2004/058911); electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides and the like (for example according to WO 2005/084081 and WO 2005/084082); atropisomers (e.g. according to WO 2006/048268); boric acid derivatives (e.g. according to WO 2006/117052); or benzanthracene (e.g. according to WO 2008/145239). Particularly preferred matrix materials are selected from: an oligoarylene group comprising naphthalene, anthracene, benzanthracene, and/or pyrene, or atropisomers of these compounds; an oligomeric arylene ethylene subunit; a ketone; phosphine oxide; and sulfoxides. Very particularly preferred matrix materials are selected from: an oligoarylene group comprising anthracene, benzanthracene, benzophenanthrene and/or pyrene, or atropisomers of these compounds. An arylene group in the sense of the present invention is intended to be understood as meaning a compound in which at least three aryl or arylene groups are bonded to one another.

The general preferred classes of materials used as the respective functional materials in the organic electroluminescent device according to the present invention are as follows.

Suitable charge transport materials that can be used in the hole injection or hole transport layer or electron blocking layer or electron transport layer of the electronic device according to the invention are compounds, for example, as disclosed in y.shirota et al, chem.rev.2007,107 (4), 953-1010, or other materials are used in these layers according to the prior art.

Materials that can be used for the electron transport layer are all materials that are used as electron transport materials in the electron transport layer according to the prior art. Particularly suitable are aluminum complexes such as Alq ₃ Zirconium complexes such as Zrq ₄ Lithium complex such as LiQ, benzimidazole derivative, triazine derivative, pyrimidine derivative, pyridine derivative, pyrazine derivative, quinoxaline derivative, quinoline derivative,Diazole derivatives, aromatic ketones, lactams, boranes, phosphodiazepine derivatives and phosphine oxide derivatives. Further suitable materials are derivatives of the above compounds as disclosed in JP 2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO 2010/072300.

Preferred hole transporting materials that can be used in the hole transporting, hole injecting or electron blocking layer in the electroluminescent device according to the invention are indenofluorene amine derivatives (e.g. according to WO 06/122630 or WO 06/100896), amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (e.g. according to WO 01/049806), amine derivatives containing a fused aromatic ring (e.g. according to US 5,061,569), amine derivatives disclosed in WO 95/09147, mono-benzindene fluorenamines (e.g. according to WO 08/006449), dibenzoindenofluorene amines (e.g. according to WO 07/140847), spirobifluorene amines (e.g. according to WO 2012/034627 or WO 2013/120577), fluorenamines (e.g. according to applications EP 2875092, EP 2875699 and EP 2875004), spirodibenzopyranamines (e.g. according to WO 3212013/086) and dihydro-acridine derivatives (e.g. according to WO/2012). The compounds according to the invention can also be used as hole transport materials.

The cathode of the organic electroluminescent device preferably comprises a metal having a low work function, a metal alloy, or a multilayer structure comprising a plurality of metals, such as alkaline earth metals, alkali metals, main group metals, or lanthanoids (e.g., ca, ba, mg, al, in, mg, yb, sm, etc.). Also suitable are alloys comprising alkali metals or alkaline earth metals and silver, for example alloys comprising magnesium and silver. In the case of a multilayer structure, other metals having a relatively high work function, such as Ag or Al, can be used in addition to the metals, in which case combinations of the metals, such as Ca/Ag, mg/Ag or Ag/Ag, are generally used. It may also be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between the metal cathode and the organic semiconductor. Suitable for this purpose are, for example, alkali metal fluorides or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g.LiF, li ₂ O、BaF ₂ 、MgO、NaF、CsF、Cs ₂ CO ₃ Etc.). In addition, lithium quinolinate (LiQ) can also be used for this purpose. The layer thickness of the layer is preferably 0.5 to 5nm.

The anode preferably comprises a material having a high work function. The anode preferably has a work function greater than 4.5eV relative to vacuum. Suitable for this purpose are metals with a high redox potential, such as, for example, ag, pt or Au. On the other hand, metal/metal oxide electrodes (e.g., al/Ni/NiO _x 、Al/PtO _x ) May also be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent to facilitate irradiation of organic material (organic solar cells) or outcoupling of light(OLED, O-laser). The preferred anode material herein is a conductive mixed metal oxide. Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO) is particularly preferred. Preference is also given to electrically conductive doped organic materials, in particular electrically conductive doped polymers.

The device (depending on the application) is suitably structured, contacts are provided and finally sealed, since the lifetime of the device according to the invention is reduced in the presence of water and/or air.

In a preferred embodiment the organic electroluminescent device according to the invention is characterized in that one or more layers are applied by sublimation, wherein the material is in a vacuum sublimation apparatus at less than 10 ^-5 mbar, preferably less than 10 ^-6 The initial pressure of mbar is applied by vapor deposition. However, it is also possible here for the initial pressure to be much lower, for example less than 10 ^- ⁷ mbar。

Preference is likewise given to organic electroluminescent devices which are characterized in that one or more layers are applied using the OVPD (organic vapor deposition) method or by means of carrier gas sublimation, with the method being carried out at 10 ^-5 The material is applied at a pressure of mbar to 1 bar. One special case of this process is the OVJP (organic vapor jet printing) process, in which the material is applied directly through a nozzle and is thereby structured (e.g. m.s. arnold et al, appl. Phys. Lett.2008,92,053301).

Furthermore, organic electroluminescent devices are preferred, which are characterized in that one or more layers are produced from a solution, for example by spin coating, or by any desired printing method, for example screen printing, flexography, nozzle printing or offset printing, but LITI (photoinitiated thermal imaging, thermal transfer) or inkjet printing are particularly preferred. For this purpose, soluble compounds of formula (I) are required. High solubility can be achieved by appropriately substituting the compounds.

Hybrid methods are also possible, in which one or more layers are applied, for example from solution, and one or more other layers are applied by vapor deposition. Thus, for example, the light-emitting layer can be applied from solution and the electron transport layer can be applied by vapor deposition.

These methods are generally known to the person skilled in the art and can be applied to organic electroluminescent devices comprising the compounds according to the invention without inventive effort.

According to the invention, electronic devices comprising one or more compounds according to the invention can be used in displays, as light sources in lighting applications, and as light sources in medical and/or cosmetic applications (e.g. phototherapy).

The invention will now be explained in more detail by the following examples without wishing to limit the invention thereby.

Synthetic examples

a) Body H1

The synthesis of the host of formula (H1) is known to the person skilled in the art and is described, for example, in WO 2010/135395, WO 2019/065415 and WO 2020/096053. Other synthetic examples are as follows:

synthesis of H1-1

10g (19.7 mmol) of 7-ethyl-4- (10-phenylanthracen-9-yl) benzanthracene are dissolved in 230mL of toluene-D8. 10.4ml (0.12 mol) of trifluoromethanesulfonic acid are added dropwise and the mixture is stirred at room temperature. After two hours, 47ml of D was added ₂ O, and the mixture was stirred for 10 minutes until it was added to the aqueous potassium phosphate solution. The mixture was extracted with toluene and the combined organic phases were dried over sodium sulfate. The organic phase is concentrated under reduced pressure. The remaining solid was purified by column chromatography and several crystallizations of dichloromethane, cyclohexane and toluene, n-heptane until the HPLC purity was 99.9% and the yield was 5.7g (10.8 mmol, 55%).

The following compounds can be synthesized in a similar manner:

synthesis of H1-3:

15g (38 mmol) of 8-bromo-dibenzofuran-1-yl triflate, 34.9g (114 mmol) of 2414494-83-8 (WO 2020071478), 35.5g (167 mmol) of potassium phosphate and 1.6g (1.9 mmol) of XPhos Palladacycle Gen.3 are dissolved in 450ml THF/water (2:1). The mixture was stirred at 90℃for 16 hours. After cooling to room temperature, 300ml of ethanol was added and the mixture was stirred for 1 hour. The precipitate was filtered and washed with ethanol. The starting material was dissolved in toluene and filtered through a filter plug (silica, toluene) to give a yellow solid, which was then further purified by several crystallizations of toluene/heptane to give a pale yellow solid (HPLC>99.9). By sublimation (at 330 ℃ C. 10) ^-5 bar) to remove the remaining solvent.

Yield: 14.1g (20.4 mmol; 54%)

Synthesis of H1-5

The oven dried flask was equipped with a magnetic stirring bar, 1 (2417686-30-5) (13.0 g,36.9mmol,1.0 eq.), 2 (237545-68-9) (18.4 g,54 mmol), tris (dibenzylideneacetone) dipalladium (1.3 g,1.4 mmol), SPhos (1.16 g,2.8 mmol) and potassium fluoride (5.3 g,92.3 mmol) under an argon atmosphere. Toluene (150 mL), 1, 4-Di were addedAlkane (150 mL) and water (150 mL), and the mixture was refluxed overnight. The crude product was purified by column chromatography and sublimation. The desired product was isolated as a white solid (5.1 g,8.9mmol, 24%).

a) Body H2

The synthesis of the host of formula (H2) is known to the person skilled in the art and is described, for example, in WO 2009/100925, WO 2018/150832 and KR 2018131963. Other synthetic examples are as follows:

synthesis of compound H2-1:

7.9g (32 mmol) of 3, 6-dichlorophenanthrene (20851-90-5), 30.4g (80 mmol) of 4, 5-tetramethyl-2- (10-phenyl-9-anthryl) -1,3, 2-dioxaborolan (460347-59-5), 29.5g (128 mmol) of potassium phosphate monohydrate are dissolved in 750ml of THF/water (2:1). 813mg (0.96 mmol) of XPhos Palladacycle Gen.3 are added and the mixture is stirred at 65 ℃. After 16 hours, the reaction mixture was allowed to reach room temperature. The reaction mixture was filtered and washed with cold tetrahydrofuran. The precipitate was purified by thermal extraction with alumina (toluene) and further purified by crystallization of toluene/ethanol and toluene/heptane until it reached that as measured by HPLC>99.9. By heating at 300℃and 10 ℃ ^-5 Tempering at bar was carried out for 2 hours to remove the remaining solvent.

Yield: 4.9g (7.2 mmol, 23%) of a pale yellow solid

The following compounds can be synthesized in a similar manner:

OLED fabrication

a) Preparation of films and devices

The glass substrate covered with pre-structured ITO (50 nm) and pixel isolation bevel construction material was cleaned using ultrasonic waves in deionized water. The substrate was then dried using an air gun and subsequently annealed on a hot plate at 230 ℃ for 2 hours.

All the following process steps were carried out under yellow light.

Fig. 4a and 4b show the following layer sequence.

A Hole Injection Layer (HIL) was ink-jet printed onto the substrate to a thickness of 20nm and dried in vacuo. For this purpose, the solids concentration of the HIL ink was 6g/l. The HIL was then annealed at 220℃for 30 minutes. The ink jet printing and annealing of the HIL were performed in air. As HIL materials, a hole transporting crosslinkable polymer and a p-doped salt were dissolved in 3-phenoxytoluene. Materials are described in WO2016/107668, WO2013/081052 and EP 2325190.

On top of the HIL, the hole transport layer was ink jet printed under ambient conditions, dried in vacuo and annealed in an argon atmosphere at 225 ℃ for 30 minutes. The hole transport layer is a polymer having the structure shown in Table 1 (HTM 1) synthesized according to WO2013156130 or a polymer HTM2 synthesized according to WO2018/114882 (Table 1).

The polymer was dissolved in 3-phenoxytoluene so that the solution generally had a solids content of about 5g/l, if the solids content is as shown herein, a typical layer thickness of 20nm for the device would be achieved by inkjet printing.

The light emitting layer comprises a host material (one host compound or two host compounds) and a dopant, as described in table 2 below. The mixture for the light emitting layer was dissolved in 3-phenoxytoluene. The solids content of this solution was about 10mg/ml, and if the solids content is as shown herein, a typical layer thickness of 30nm for the device would be achieved by inkjet printing. The blue light emitting layer (B-EML) was also ink jet printed, then vacuum dried and annealed at 150 ℃ for 10 minutes. Inkjet printing was done in an ambient atmosphere, while annealing was done in an argon atmosphere.

The device prepared according to fig. 4a was used to evaluate the uniformity of the EML film.

To prepare a device for electro-optical characterization according to fig. 4b, the sample was transferred into a vacuum deposition chamber where deposition of the two electron transport layers (ETL 1, ETL 2), electron Injection Layer (EIL) and cathode (Al) was accomplished using thermal evaporation. Thus, ETL1 was composed of ETM1 (film thickness of 10 nm), while ETL2 was composed of a 1:1 volume% mixture of ETM1 and ETM2 (film thickness of 35 nm). The electron injection layer consisted of ETM2 (1 nm) and the cathode was aluminum (100 nm). The structure is shown in table 1.

After evaporation, the device was packaged in a glove box in an argon atmosphere.

Table 1: material structure of the solution treatment layer.

b) Evaluation of uniformity of luminescent film

It is important for the manufacture of displays to obtain very good pixel uniformity while achieving good device performance. The uneven layer thickness causes uneven luminance distribution in which thinner film thickness regions show an increase in luminance and thicker regions show a decrease in luminance. Such unevenness varies from pixel to pixel, thereby impeding a reproducible appearance between pixels. In summary, this will lead to a negative view of the quality of such displays. Accordingly, the present invention addresses the subject of EML film uniformity and device performance. Thus, the first step in the evaluation is to check the film uniformity. For this purpose, a laminate structure as shown in fig. 4a is used. The process is stopped after EML deposition. The film was prepared as described in part a). The composition of the EML is shown in tables 2a and 2 b.

To evaluate the uniformity of the printed film, a profiler was used to characterize its topography along a 10 μm profile and R was calculated _p-v (peak to valley) value and root mean square deviation of roughness. Film profile was measured using a profiler Alpha-step D120 of KLA-Tencor Corporation and a 2 μm stylus. R is R _p-v The values correspond to the difference in height between the maximum peak and the minimum peak measured within the measured profile. For ease of observation, the baseline of the film profile was subtracted, with the minimum peak corresponding to a height of 0nm and the axis scale of all figures being the same.

The following two equations are used to determine film uniformity. Peak-valley difference R _p-v Representing the maximum height difference (equation 1) within a layer, root mean square roughness RMS, where z _i Corresponds to the profile height at position i andcorresponding to the average profile height (equation 2).

R _p-v =rp-Rv equation 1

Table 2a. Film profile and corresponding figures.

Example PE1 comprising a host mixture according to the invention shows a significantly reduced R compared to PR1 _p-v And RMS value, only bulk component 2 was used in the PR1, thus corresponding to smoother films (fig. 1 and 3).

In addition, example PE1 shows a similar R as reference PR2 _p-v And RMS values, it also resulted in significantly better OLED performance, as shown in table 5a (DE 1 vs DR 1).

In summary, only the hybrid host system can achieve both smooth films with good uniformity and good device performance (EQE and LT).

Other film uniformity for other light emitting layers (EML) are shown in table 2b.

TABLE 2b other film profiles

In the case of all light-emitting layer profiles based on a mixed host system, EML, R relative to the individual host based on host component 1 _p-v And significantly lower RMS values (PE 2 vs. PR4, PE3 vs. PR6, PE4 vs. PE5 vs. PR8, PE6 vs. PR10, PE7 vs. PR 12). R of EML (Mixed host System) according to the invention compared to the individual EML based on Single host component 2 _p-v And RMS values are in a similar range. In these cases, the advantage of the present invention is better device performance (EQE or LT), as shown in the device results section below (see tables 5 a-e).

c) Device results

As shown in fig. 4b, a device is prepared according to part a). The host materials are shown in table 3 and the emitters are shown in table 4. Blue EML inks were mixed according to tables 5a-e and tables 6 a-c.

To determine the device performance of the prepared OLED, it was characterized using standard methods. For this purpose, electroluminescence spectra, current/voltage/optical density characteristic curves (IUL characteristic curves) (assuming Lambert luminescence characteristics) and (operating) lifetimes are recorded. The IUL characteristic curve is an index map for determining, for example, the external quantum efficiency (in%) at a specific luminance. The device is driven with a constant voltage at each step of the applied voltage ramp. The device lifetime is measured at a given current corresponding to the initial brightness. The change in luminance over time is then measured by means of calibrated photodiodes.

In tables 5a-e, the relative external quantum efficiencies of the EMLs whose profiles are studied in tables 2a and 2b are summarized (1000 cd/m ² Relative EQE at time) and relative device lifetime (1000 cd/m ² Relative LT90 at that time).

Table 3: main body structure

Table 4: luminous body structure

Table 5a: blue EML mixture for device embodiments with 1% E2

Table 5b: blue EML mixture for device example with 5% E4

Table 5c: blue EML mixture for device example with 3% E1

Table 5d: blue EML mixture for device embodiments with 3% E3

Table 5e: blue EML mixture for device embodiments with 2% E2

Table 5f: blue EML mixture for device example with 5% E3

All of the illustrated embodiments of the hybrid host system exhibit improved device performance compared to the individual unitary host EMLs based on host component 2. The device performance of the hybrid host system is approximately comparable to that of the single host EML based on host component 1. However, in these cases, as shown in tables 2a and 2b, improved film uniformity was obtained.

In summary, the present invention (i.e., mixed host EML) achieves both smooth films with good uniformity and good device performance (EQE and LT).

Other mixed host EML examples with good film uniformity and good device performance are summarized in tables 6 a-c.

Table 6a: blue EML mixture for device embodiments with 3% E2

Table 6b: blue EML mixture for device example with 1% E1

Table 6c: blue EML mixture for device example with 3% E1

Claims

1. A composition for a light emitting layer, the composition comprising:

a first host material of formula (H1)

A second host material of formula (H2)

And a dopant material;

wherein the coincidence and notation used applies as follows:

G ₁ is an aromatic or heteroaromatic ring system having from 6 to 60 aromatic ring atoms, which may be bound in each case by one or more radicals R ^X Substitution;

G ₂ a group selected from formula (G2):

wherein the group E is selected from-Y=Y-, -C (R ^B0 ) ₂ -、-Si(R ^B0 ) ₂ -、-O-、-S-、-C(＝O)-、-S(＝O)-、-SO ₂ -、-BR ^B0 -、-N(R ^B0 ) -or-P (R) ^B0 ) -a divalent bridging group in; and wherein R is ^B0 Identically or differently on each occurrence represents: h, F, CN, having from 1 to 40 linear alkyl groups or having from 3 to 40 branched or cyclic alkyl groups, each of which may be substituted by one or more groups R, having from 5 to 60 aromatic or heteroaromatic ring systems which may in each case be substituted by one or more groups R; wherein two adjacent substituents R ^B0 An aliphatic or aromatic ring system which may be mono-or polycyclic and which may be substituted by one or more radicals R;

Ant ₁ is a group of formula (A1):

Ant ₂ is a group of formula (A2):

Ar ^A1 、Ar ^B1 、Ar ^AS 、Ar ^BS identically or differently at each occurrenceAn aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which may also be substituted in each case by one or more radicals R;

R ^A1 to R ^A8 、R ^B1 To R ^B8 、R ^Y 、R ^X Represents, identically or differently on each occurrence, a group selected from: h, D, F, cl, br, I, CHO, CN, C (=O) Ar, P (=O) (Ar) ₂ ，S(＝O)Ar，S(＝O) ₂ Ar，N(R) ₂ ，N(Ar) ₂ ，NO ₂ ，Si(R) ₃ ，B(OR) ₂ ，OSO ₂ R, a linear alkyl, alkoxy or thioalkyl radical having from 1 to 40C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40C atoms, which radicals may each be substituted by one or more radicals R, where in each case one or more non-adjacent CH ₂ The radicals may be substituted by RC=CR, C≡ C, si (R) ₂ 、Ge(R) ₂ 、Sn(R) ₂ 、C＝O、C＝S、C＝Se、P(＝O)(R)、SO、SO ₂ O, S or CONR and wherein one or more H atoms may be replaced by D, F, cl, br, I, CN or NO ₂ Alternatively, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, and an aryloxy group having from 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R;

provided that R ^B1 To R ^B8 And R is ^Y Not representing D; and is also provided with

Wherein two adjacent radicals R ^A1 To R ^A8 、R ^B1 To R ^B8 、R ^Y Or R is ^X May together form an aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more groups R;

r, identically or differently at each occurrence, represents: h, D, F, cl, br, I, CHO, CN, C (=O) Ar, P (=O) (Ar) ₂ ，S(＝O)Ar，S(＝O) ₂ Ar，N(R') ₂ ，N(Ar) ₂ ，NO ₂ ，Si(R') ₃ ，B(OR') ₂ ，OSO ₂ R 'is a linear alkyl, alkoxy or thioalkyl radical having from 1 to 40C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 40C atoms, which radicals may each be substituted by one or more radicals R', where in each case one or more non-adjacent CH ₂ The radicals may be substituted by R ' C=CR ', C≡ C, si (R ') ₂ 、Ge(R') ₂ 、Sn(R') ₂ 、C＝O、C＝S、C＝Se、P(＝O)(R')、SO、SO ₂ O, S or CONR' and wherein one or more H atoms may be replaced by D, F, cl, br, I, CN or NO ₂ Alternatively, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R ', an aryloxy group having from 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R'; wherein two adjacent groups R may together form an aliphatic or aromatic ring system, which may be substituted with one or more groups R';

r' represents identically or differently on each occurrence: h, D, F, cl, br, I, CN, a linear alkyl, alkoxy or thioalkyl radical having from 1 to 20C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having from 3 to 20C atoms, where in each case one or more non-adjacent CH ₂ The radicals may be replaced by SO, SO ₂ O, S, and wherein one or more H atoms may be replaced by D, F, cl, br or I, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms; and is also provided with

m is 0 or 1;

2. The composition as claimed in claim 1, wherein the group G ₁ A group selected from the group consisting of:

wherein:

E ⁵ representative-BR ⁰ -、-C(R ⁰ ) ₂ -、-Si(R ⁰ ) ₂ -、-C(＝O)-、-O-、-S-、-S(＝O)-、-SO ₂ -、-N(R ⁰ ) -or-P (R) ⁰ )-；

R ⁰ Identically or differently on each occurrence represents: h, D, F, CN, a linear alkyl group having from 1 to 40C atoms or a branched or cyclic alkyl group having from 3 to 40C atoms, each of which may be substituted by one or more radicals R, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, which is present in various forms In case it may be substituted by one or more groups R; wherein two adjacent substituents R ⁰ An aliphatic or aromatic ring system which may be mono-or polycyclic and which may be substituted by one or more radicals R;

R ^X r has the same meaning as in claim 1.

3. Composition according to claim 1 or 2, characterized in that the compound of formula (H1) is chosen from the compounds of formula:

wherein the symbols have the same meaning as in claim 1 and wherein the compounds of formulae (G1-1-1) to (G1-12-3) contain at least one deuterium atom.

4. Composition according to one or more of the preceding claims, characterized in that the molecular weight of the compound of formula (H1) is Mw. Gtoreq.350 g/mol.

5. Composition according to one or more of the preceding claims, characterized in that in the compound of formula (H1) at least one deuterium atom is a group Ant ₁ Or a substituent on group G1.

6. Composition according to one or more of the preceding claims, characterized in that at least 10% of the compounds of formula (H1) are deuterated, which means that at least 10% of the available H atoms in the compounds of formula (H1) are replaced by deuterium atoms.

7. Composition according to one or more of the preceding claims, characterized in that said compound of formula (H1) is present in said composition in a proportion equal to or higher than 1% by weight of the composition.

8. Composition according to one or more of the preceding claims, characterized in that the group G ₂ A group selected from the group consisting of:

wherein:

y represents C-R identically or differently on each occurrence ^Y Or N; provided that when Y is the same as the group Ant ₂ Y represents C when bonded; and wherein the symbol R ^Y And R is ⁰ Has the same meaning as in claim 1.

9. Composition according to one or more of the preceding claims, characterized in that said compound of formula (H2) is chosen from the groups of formula:

wherein the symbols have the same meaning as in claim 1.

10. Composition according to one or more of the preceding claims, characterized in that the compound of formula (H2) is present in the composition in a proportion equal to or higher than 1% by weight of the composition.

11. Composition according to one or more of the preceding claims, characterized in that the group Ar ^A1 And Ar is a group ^B1 Selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorene, spirobifluorene, naphthalene, anthracene, phenanthrene, triphenylene, fluoranthene, naphthacene, chicory, benzanthracene, benzophenanthrene, pyrene or perylene, dibenzofuran, carbazole and dibenzothiophene, each of which may be substituted in any free position by one or more radicals R; and wherein Ar is ^A1 、Ar ^B1 Combinations of two or more of the foregoing groups are also possible.

12. Composition according to one or more of the preceding claims, characterized in that the dopant material is a fluorescent emitter.

13. The composition according to one or more of the preceding claims, characterized in that said dopant material is a fluorescent emitter selected from the group consisting of:

-bridged triarylamines;

-indenofluorene, indenofluorene amine or indenofluorene diamine;

-benzindene fluorene, benzindene fluorene amine or benzindene fluorene diamine;

-bis-indenoindenofluorene;

-indenofluor, indenofluorene amine or indenofluorene diamine;

-fluorene dimers;

-a phenoneAn oxazine; and

-boron derivatives.

14. Composition according to one or more of the preceding claims, characterized in that the dopant material is a fluorescent emitter of formula (E-1), (E-2), (E-3) or (E-4),

Wherein the method comprises the steps of

r has the same definition as in claim 1; and is also provided with

e is 1, 2, 3 or 4; more preferably, e is 1;

wherein the method comprises the steps of

Ar ²⁰ 、Ar ²¹ 、Ar ²² Identically or differently on each occurrence are aryl or heteroaryl groups having 6 to 30 aromatic ring atoms, which may also be substituted in each case by one or more radicals R;

E ²⁰ at each timeIs selected from BR, C (R ⁰ ) ₂ 、Si(R ⁰ ) ₂ 、C＝O、C＝NR ⁰ 、C＝C(R ⁰ ) ₂ 、O、S、S＝O、SO ₂ 、NR ⁰ 、PR ⁰ 、P(＝O)R ⁰ Or P (=S) R ⁰ The group in (a); wherein Ar is ²⁰ 、Ar ²¹ And E is ²⁰ Together form a five-membered or six-membered ring, and Ar ²¹ 、Ar ²³ And E is ²⁰ Together forming a five-membered or six-membered ring;

R ⁰ identically or differently on each occurrence represents: h, D, F, a linear alkyl group having from 1 to 20, preferably from 1 to 10, C atoms or a branched or cyclic alkyl group having from 3 to 20, preferably from 3 to 10, C atoms, which groups may each be substituted by one or more groups R, where in each case one or more non-adjacent CH ₂ The radicals may be replaced by O or S and one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having from 5 to 40, preferably from 5 to 30, more preferably from 6 to 18, aromatic ring atoms, which may in each case be substituted by one or more radicals R, two adjacent radicals R ⁰ May together form an aliphatic or aromatic ring system which may be substituted by one or more groups R,

r has the same definition as in claim 1;

r is 1, 2 or 3;

wherein the method comprises the steps of

E ³⁰ representative ofB or N;

R ⁰ Having the same definition as above;

Wherein the method comprises the steps of

R ⁰ having the same definition as above;

15. A formulation comprising a composition according to one or more of claims 1 to 14 and at least one solvent.

16. A method of manufacturing an electronic device comprising at least one layer comprising a composition according to one or more of claims 1 to 14, the method comprising the steps of:

a) Preparing a formulation comprising a composition according to one or more of claims 1 to 14 and at least one solvent;

b) Applying the formulation prepared in step a) to a substrate or another layer to form a layer;

c) The layer is dried to remove the solvent.

17. The method of claim 16, wherein the formulation is applied by a coating process or a printing process.

18. The method of claim 16 or 17, wherein the formulation is applied by flow coating, dip coating, spray coating, spin coating, screen printing, letterpress printing, gravure printing, roll coating, ink jet printing, rotary printing, flexography, offset printing, slot die coating, or nozzle printing.

19. An organic electroluminescent device, the organic electroluminescent device comprising:

an anode;

a cathode;

at least one light emitting layer between the anode and the cathode, wherein the light emitting layer between the anode and the cathode comprises a composition as defined in claims 1 to 14.

20. The organic electroluminescent device according to claim 19, wherein the light emitting layer does not comprise a phosphorescent light emitter as dopant material.